Preparation of 5-substituted 3-aminofuran-2-carboxylate esters

被引：32

作者：

Redman, AM ^{[1
]}

Dumas, J ^{[1
]}

Scott, WJ ^{[1
]}

机构：

[1] Bayer Res Ctr, Dept Chem Res, W Haven, CT 06516 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 14期

关键词：

D O I：

10.1021/ol0059652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS An efficient method for the preparation of 3-aminofuran-2-carboxylate esters has been developed. This method is based on the reaction of an alpha-cyanoketone with ethyl glyoxylate under Mitsunobu conditions to produce a vinyl ether in good yield. Subsequent treatment of the vinyl ether with sodium hydride afforded the 3-aminofuran, It was also found that a one pot procedure using the Mitsunobu reaction followed by cyclization afforded the 3-aminofuran in comparable yield. Currently, this method is limited to the synthesis of 5-alkyl-, 5-aryl-, and 4,5-fused bicyclic furans.

引用

页码：2061 / 2063

页数：3

共 9 条

[1] REGIOSPECIFIC O-ALKYLATION OF BETA-TETRONIC ACIDS UNDER MITSUNOBU REACTION CONDITIONS [J].